Explosive.



HAROLD HIBBERT, 0F

NEMOURS POWDER COMPANY, NEW JERSEY.

WILMINGTON, DELAWARE,

OF WILMINGTON,

ASSIGNOR TO E. I. DU PONT DE DELAWARE, A CORPORATION OF EXPLOSIVE.

No Drawing.

To all whom it may concern: 4

Be it known that I, HAROLD HIBBER'I, a subject of the King of Great Britain, residing at \Vilmington, county of Newcastle, and State of Delaware, have invented a new and useful Improvement in Explosives, of which the following is a full, clear, and exact description.

lVhen glycerin is treated with the mixed acids, nitric acid and sulfuric acid, for the production of glycerin trinitrate, glycerin trinitrate is produced, the formula of which 15' onazoa (in NO- HzNOa This glycerin trinitrate has certain defects, among which it may be stated that the glycerin which is its base is expensive, and the temperature of explosion of the explosive mixture of the glycerin trinitrate is very high, which makes it in many cases not a good ingredient for smokeless powder. I have discovered that if nitrated butylene glycol be formed, a product is obtained whose temperature of explosive ignition is lower than that of glycerin trinitrate, which enables it to be freely used as an ingredient of smokeless powder, safety explosives and dynamite. Further, I have discovered that such compound may be combined with nitrated derivatives, such, for instance, as nitrated cellulose or nitrated starch, to form a colloid of such mixtures. It also may be mixed with glycerin trinitrate, and the resulting mixture has a lower freezing point and is more stable than glycerin trinitrate.

While butylene glycol is known and is described in text books, I believe myself to be the first to have discovered nitratedl butylene glycol and its value for the purposes named. Further, the method of making butylene glycol, as set out in the text books, is so complicated as to render it very expensive and difficult to carry out. My discovery, therefore, includes a simple method for directly producing this butylene glycol as well as the nitrated butylene glycol.

Specification of Letters Patent. Patented June 13 1911 Application filed September 15, 1910. Serial No. 582,145.

The butylene glycol is represented in formula in the following manner:

CHa-CH OH CH: (lHsOH and when nitrated the formula is thus represented:

cn3 crr N03 HzNOg I produce the butylene glycol in the following manner: I take ethyl alcohol (GJLOH), which may be de-natured without affecting the result. This ethyl alcohol is first oxidized. Preferably I accomplish this oxidation by the ordinary catalytic oxidation, such for instance, by using metallic plat num, copper or zinc and heat. The resultant is acetaldehyde (C. ,H,O). This acetaldehyde is then condensed. I have used for this condensation an aqueous solution of an alkaline carbonate, for instance, potassium carbonate; 450 grams of acetaldehyde were cooled to -5 C. and 200 grams of powdered ice then added. A few drops of a cooled solution of potassium carbonate containing 19 grams of the carbonate in 60 cubic centimeters of water were introduced into this mixture, the temperature not being allowed to rise above +10 C. After standing some 10 or 15 minutes a further quantity of the carbonate solution was introduced and again allowed to stand, contents being kept as nearly as possible at a temperature of 0 C. After the whole of the carbonate had been added, the reactionproduct was kept in ice-water for several hours to prevent any rise of temperature and then for a further 20 hours at +8 to +10 C. If the pure acetaldol is required this may be extracted with ether, but for the purpose of obtaining butylene glycol this is unnecessary. The condensation can be pro duced by other alkaline carbonate of a borate, phosphate, acetate or cyanid, of the alkaline metals or alkaline earths. The resultant of this condensation is acetaldol (QH O This condensation product is tion, the butylene then-reduced to butylene glycolby' means of a reducing agent, and I have employed the following method: The aqueous solution of acetaldol, obtained by condensing 450 grams.

of' acetaldehyde with potassium carbonate was diluted to six liters with ice-water, ren-- or an alloy or several metals may be used the use of mercury. In-

and also w thout this condition the butylene glycol exists in an aqueous solution and is isolated by simple distillation, preferably under vacuum. This butylene glycol may then be nitrated in the same manner that glycerin is nitrated, by means of nitric acid and sulfuric acid, in the following manner: 350 grams' of or.-

dinary nitrating acid such as is used for the nitration ofglycerin were cooled to 5 C. and then 50 grams of butylene glycol slowly introduced into this, under the surface of the liquid in a fine spray, the acid being ke t at 5 C. and agitated vigorously throug out the addition. The butylene glycol dinitrate at once rises to the surface as a yellow oil and may be separated without further difliculty from the acid mixture. The resultant nitrated compound may then be used by itself or mixed with a nitrate or nitrates, such as nitrated cellulose or nitrated starch. Indeed, I have found it quite valuable when mixed with glycerin trinitrate,

Copies of this patent may be obtained for five cents each,v by addressing the Washington, D. 0.

mixture left for a' After filtering the solu- .Nor do I claim herein ducing butylene glycol,'herein described, as

the formula of the glycerin trinitrate. like manner, when I use the term nitrated or nitro compounds, as, for instance, tetrani'tro-methane, tri-nitrotoluene, nitro-naphthalene, or tri-nitro-anisoh Examples of such mixtures which may be used, are 80 parts by weight of butylene glycol nitrate -When I speak of glycerin trinitrate, of

course I intend to include the glycerin'monoand di-nitrates,although I have shown only butyleneglycOl I intend to include the butylene glycol mono-nitrate and the butylene glycol dinitrate, although I have only shown the formula of the butylene glycol dinitrate.

, I'do not claim hereineither' the butylene glycol nitrate alone or mixed with a nitrate or nitrates as the same forms the subject matter of the claims of an application filed by me June 15th, 1910, Serial No. 566,934.

the method of prothat is claimed in an application filed by me September 15th, 1910, Serial No. 582,144.

'Having now fully described my invention, what I claim and desire to protect by Letters Patent is:

- 1. An explosive containing an admixture of butylene glycol nitrate and a nitro compound.

2. An explosive containing an admixture of butylene glycol nitrate and nitro compounds.

In testimony of which invention,

hereunto set my hand, at Wilmington, Del. I

on this 10th day of Sept, 1910.

HAROLD HIBBERT.

as it then lowers the freezing point of glyc- Witnesses: erin trinitrate. Butylene gylcol dinitrate J. ED. WILsoN,

may also be mixed with a nitro compound J. A. CASEY.

Commissioner of Patents, 

